Water → HCID 77977979, compound

HRID 1023432Notes

Reaction equation

HRID 1023432 reaction equation
[C:1]([O:5][C:6](=[O:26])[NH:7][C:8]1[CH:13]=[C:12]([CH2:14][C:15]([CH:23]2[CH2:25][CH2:24]2)(O)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:11]=[CH:10][N:9]=1)([CH3:4])([CH3:3])[CH3:2].S(Cl)(Cl)=O.C([O-])(O)=O.[Na+].O>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[C:1]([O:5][C:6](=[O:26])[NH:7][C:8]1[CH:13]=[C:12]([CH:14]=[C:15]([CH:23]2[CH2:24][CH2:25]2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:11]=[CH:10][N:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 962WaterHCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 71000664[4-(2-Cyclopropyl-2-hydroxy-2-phenyl-ethyl)-pyridin-2-yl]-carbamic acid tert-butyl ester

Product 1

HCID 77977979HCID 77977979, compoundYield 35.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

[4-(2-Cyclopropyl-2-hydroxy-2-phenyl-ethyl)-pyridin-2-yl]-carbamic acid tert-butyl ester (280 mg, 0.79 mmol) and 4-dimethylaminopyridine (97 mg, 0.79 mmol) are dissovled in pyridine (3.0 mL) and thionyl chloride (0.12 mL, 1.6 mmol) is added at 0° C. After the mixture is stirred for 3 hrs at room temperature, saturated NaHCO3 aqueous solution (4 mL) is added along with water (20 ml). The mixture is extracted with EtOAc (3×25 mL) and the organic layers are combined and concentrated to give the crude product. Purification by silica flash column chromatography using MeOH in DCM (gradient from 0% to 6%) affords 94 mg of the desired product.

Workup

  1. extractionThe mixture is extracted with EtOAc (3×25 mL)
  2. concentrationconcentrated
  3. customto give the crude product
  4. customPurification by silica flash column chromatography

Sources & evidence

ORD record
ord-cbc1bb2e8d444720b96b10484e5f93ea
Source dataset
uspto-grants-2014_05
Patent number
US08722709B2

Reaction notes

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